When I went down with my daughter in May, we stayed at the Fairfield Inn by Marriott. We got a good deal for $47 but they are now around $80 I think. The Holiday Inn Sunspree is also very close but I think it's also not cheap.
The best hotel deals I have found online are at lastminutetravel.com The Econolodge Polynesian is now offered for $29 a night. It's about 4 miles away but easy to drive back and forth. Print up maps on the internet and have a good local map from your car rental place and the free magazines at most restraunts. I have found their maps to be pretty good.
A lot of parents stayed at Disney's All Star Resort too. One I know stayed there and took a cab back and forth but it's better to rent a car. Check Costco for discounts. Some car rental co's have quick check in 'clubs' for free, it helps to join to avoid waiting in line for two hours as I did at Budget on a weekend. Weekdays aren't bad. Now I'm a Fastbreak member and I won't have to stand in line next time when I go visit (and become broke again).
We also went shopping at Target,Walmart and Publix to stock her up. Funny that you talk of getting a loan for this thing. I spent $500 for groceries and supplies. But I bought her 7 months worth of nonperishables, bathroom stuff, a lamp, a large trash can for the kitchen, etc. A lot of parents let the kids buy their own stuff. I just started her out and she is now buying her own groceries. But I have sent her some things like socks, when I found out she was recycling the same 3 pair of black socks all week for work. Funny how when it's their money how thrifty they can be.
I also send my daughter coupons and she says she's doing well at spotting bargains. SHe likes to buy frozen dinners to take to work since it's cheaper than eating there. They also get 20% off at the Disney eateries on property. The McDonalds at Downtown Disney as well as most all their restraunts offer the CP's the discount. My daughter doesn't like to cook either and they hardly have time to anyway. But she does occasionally make hamburger helper and mac and cheese sorts of meals and salads and sandwiches.
If you go down the night before maybe you could find a meet and greet. My daughter and I met with about 10 or more cp's at Planet Hollywood, where she met her roommates. They arranged to meet the next morning and checked in together. Here's a website to find a possible meet and greet, or he can arrange one there. These are informal and totally separate from Disney.
http://www.wdwcpinfo.com/
My daughter also doesn't have a car down there and doesn't mind taking the bus. It's time for her to make cell phone calls home or close her eyes or read a book when she's not meeting new people on it. She also has met some friends that have cars and have taken her shopping, etc. She hasn't taken a shuttle to Walmart yet as she's always found a friend who is going or just waits until she can find one. It really hasn't been a problem for her.
Ask your son if you can read thru the disney college website with his password. It's not the easiest to navigate but there's lots to read and will help you to understand more of the whole thing.
http://www.wdwcollegeprogram.com/sap.../index-ie.html
Oh yeah, when you go for check in the kids check in by themselves and the parents are sent to a tented area to wait. You can meet other parents and talk and they give out prizes and have people there to answer your questions. Then when they're done, you get to help them move in. He may be scheduled for a meeting that day. My dd checked in about an hour before the official time then had a meeting at the Commons apts at noon. So we moved stuff in and while she was in the meeting one of the other mothers and I went to Walmart and shopped. Came back, unpacked some more and went back to Walmart for another load with the other roommates. Then back to the apt to make sure her anti-virus, etc. was installed in her computer and set up and out by 1am so she wouldn't get in trouble. I am glad she checked in so early as we used the whole day. I flew home the next day and the girls hit the parks and bonded.
BTW, Southwest airlines has some really good deals to Orlando right now and they let you check more luggage than most airlnes. Do check the size/weight restrictions as the fines are very steep. We weighed the bags on a bathroom scale and moved contents from bag to bag.
Sorry for being so long winded. Have a good time!